<3S-<3α(S^*),4β>>-t-butyl 1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-carboxylate

Base Information

• Chemical Name: <3S-<3α(S^*),4β>>-t-butyl 1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-carboxylate
• CAS No.: 81902-61-6
• Molecular Formula: C₂₅H₄₁NO₆Si
• Molecular Weight: 479.689

Synonyms:<3S-<3α(S^*),4β>>-t-butyl 1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-carboxylate

Chemical Property of <3S-<3α(S^*),4β>>-t-butyl 1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-carboxylate

Chemical Property:

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Technology Process of <3S-<3α(S^*),4β>>-t-butyl 1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-carboxylate

There total 7 articles about <3S-<3α(S^*),4β>>-t-butyl 1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.7%

<3S-<3α(S*),4β>>-t-butyl 1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-2-azetidinone-4-carboxylate (80829-72-7) + tert-butyldimethylsilyl chloride (18162-48-6) → <3S-<3α(S*),4β>>-t-butyl 1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-carboxylate (81902-61-6)

Guidance literature:

With dmap; In N,N-dimethyl-formamide; at 25 ℃; for 15h;

DOI:10.1016/S0040-4039(01)92460-8

Reference yield:

(2S,3R)-N-(2,4-dimethoxybenzyl)-N-(t-butoxycarbonylmethyl)-2-bromo-3-hydroxybutyramide (81902-59-2) → <3S-<3α(S*),4β>>-t-butyl 1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-carboxylate (81902-61-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LiN(SiMe₃)2, 2.) LiN(SiMe₃)2 / 1.) THF, 15 min., from 0 deg C to 5 deg C, 2.) from 20 deg C to 25 deg C, THF, 1 h.

2: 96.7 percent / 4-dimethylaminopyridine / dimethylformamide / Ambient temperature

With dmap; lithium hexamethyldisilazane; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)91132-9

Reference yield:

bromoacetic acid tert-butyl ester (5292-43-3) → <3S-<3α(S*),4β>>-t-butyl 1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-carboxylate (81902-61-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 58 percent / Et₃N / tetrahydrofuran / 1 h / Heating

2: 84 percent / N,N-dicyclohexylcarbodiimide / tetrahydrofuran / 0.25 h / 20 - 25 °C

3: 1.) LiN(SiMe₃)2, 2.) LiN(SiMe₃)2 / 1.) THF, 15 min., from 0 deg C to 5 deg C, 2.) from 20 deg C to 25 deg C, THF, 1 h.

4: 96.7 percent / 4-dimethylaminopyridine / dimethylformamide / Ambient temperature

With dmap; triethylamine; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)91132-9

upstream raw materials:

<3S-<3α(S^*),4β>>-t-butyl 1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-2-azetidinone-4-carboxylate

tert-butyldimethylsilyl chloride

bromoacetic acid tert-butyl ester

2,4-dimethoxybenzylamine hydrochloride

Downstream raw materials:

<3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-hydroxymethyl-2-azetidinone

<3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-carboxylic acid

<3S-<3α(S^*),4β>>-benzyl<3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-yl>acetate

<3S-<3α(S^*),4β>>-benzyl<1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-yl>acetate

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